JP2012513480A5 - - Google Patents
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- JP2012513480A5 JP2012513480A5 JP2011543688A JP2011543688A JP2012513480A5 JP 2012513480 A5 JP2012513480 A5 JP 2012513480A5 JP 2011543688 A JP2011543688 A JP 2011543688A JP 2011543688 A JP2011543688 A JP 2011543688A JP 2012513480 A5 JP2012513480 A5 JP 2012513480A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- heterocyclyl
- methyl
- cycloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 116
- -1 amino, substituted amino, carboxyl Chemical group 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims description 76
- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 60
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 49
- 150000002431 hydrogen Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000003107 substituted aryl group Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 32
- 125000002252 acyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000001475 halogen functional group Chemical group 0.000 claims description 26
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 16
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 8
- 102000042838 JAK family Human genes 0.000 claims description 8
- 108091082332 JAK family Proteins 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims description 4
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 4
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 208000030533 eye disease Diseases 0.000 claims description 4
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 4
- 239000003018 immunosuppressive agent Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- SXIQFKMFFAAXGY-UHFFFAOYSA-N 3-[[4-[3-[(ethylsulfamoylamino)methyl]anilino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CCNS(=O)(=O)NCC1=CC=CC(NC=2C(=CN=C(NC=3C=C(C=CC=3)S(N)(=O)=O)N=2)F)=C1 SXIQFKMFFAAXGY-UHFFFAOYSA-N 0.000 claims description 2
- AHNPDJCFASQBGK-UHFFFAOYSA-N 3-[[4-[3-[(ethylsulfamoylamino)methyl]anilino]-5-methylpyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CCNS(=O)(=O)NCC1=CC=CC(NC=2C(=CN=C(NC=3C=C(C=CC=3)S(N)(=O)=O)N=2)C)=C1 AHNPDJCFASQBGK-UHFFFAOYSA-N 0.000 claims description 2
- XSPDAEZTNONJSE-UHFFFAOYSA-N 3-[[4-[4-[(cyclopropylsulfamoylamino)methyl]anilino]-5-methylpyrimidin-2-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=CC(CNS(=O)(=O)NC3CC3)=CC=2)C(C)=CN=C1NC1=CC=CC(S(N)(=O)=O)=C1 XSPDAEZTNONJSE-UHFFFAOYSA-N 0.000 claims description 2
- KJUKNCPBIOOPKN-UHFFFAOYSA-N 3-[[4-[4-[(ethylsulfamoylamino)methyl]anilino]-5-methylpyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(CNS(=O)(=O)NCC)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1C KJUKNCPBIOOPKN-UHFFFAOYSA-N 0.000 claims description 2
- DEUVUMACSOVDNU-UHFFFAOYSA-N 3-[[5-chloro-4-[3-[(ethylsulfamoylamino)methyl]anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CCNS(=O)(=O)NCC1=CC=CC(NC=2C(=CN=C(NC=3C=C(C=CC=3)S(N)(=O)=O)N=2)Cl)=C1 DEUVUMACSOVDNU-UHFFFAOYSA-N 0.000 claims description 2
- RGUNHWSADWWKBU-UHFFFAOYSA-N 3-[[5-chloro-4-[4-[(cyclopropylsulfamoylamino)methyl]-2-methylanilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C(NC=2C(=CN=C(NC=3C=C(C=CC=3)S(N)(=O)=O)N=2)Cl)C(C)=CC=1CNS(=O)(=O)NC1CC1 RGUNHWSADWWKBU-UHFFFAOYSA-N 0.000 claims description 2
- ZJLBMQVRVNHLKC-UHFFFAOYSA-N 3-[[5-chloro-4-[4-[(cyclopropylsulfamoylamino)methyl]anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(CNS(=O)(=O)NC4CC4)=CC=3)C(Cl)=CN=2)=C1 ZJLBMQVRVNHLKC-UHFFFAOYSA-N 0.000 claims description 2
- SXJBVMNZHJAPOR-UHFFFAOYSA-N 3-[[5-chloro-4-[4-[(ethylsulfamoylamino)methyl]-2-methylanilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CC1=CC(CNS(=O)(=O)NCC)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1Cl SXJBVMNZHJAPOR-UHFFFAOYSA-N 0.000 claims description 2
- OBCLIVGSWMZNGO-UHFFFAOYSA-N 3-[[5-chloro-4-[4-[(ethylsulfamoylamino)methyl]anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(CNS(=O)(=O)NCC)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1Cl OBCLIVGSWMZNGO-UHFFFAOYSA-N 0.000 claims description 2
- GXZPCWYGBMQFJE-UHFFFAOYSA-N 4-[[4-[3-[(ethylsulfamoylamino)methyl]anilino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CCNS(=O)(=O)NCC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=2)F)=C1 GXZPCWYGBMQFJE-UHFFFAOYSA-N 0.000 claims description 2
- UXTJYUXEEKERFB-UHFFFAOYSA-N 4-[[4-[3-[(ethylsulfamoylamino)methyl]anilino]-5-methylpyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CCNS(=O)(=O)NCC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=2)C)=C1 UXTJYUXEEKERFB-UHFFFAOYSA-N 0.000 claims description 2
- AVIUXONYUXOEQH-UHFFFAOYSA-N 4-[[4-[4-[(cyclopropylsulfamoylamino)methyl]anilino]-5-methylpyrimidin-2-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=CC(CNS(=O)(=O)NC3CC3)=CC=2)C(C)=CN=C1NC1=CC=C(S(N)(=O)=O)C=C1 AVIUXONYUXOEQH-UHFFFAOYSA-N 0.000 claims description 2
- AYZVOFAPBGXCQD-UHFFFAOYSA-N 4-[[4-[4-[(ethylsulfamoylamino)methyl]anilino]-5-methylpyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(CNS(=O)(=O)NCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1C AYZVOFAPBGXCQD-UHFFFAOYSA-N 0.000 claims description 2
- UHKFVZWCALJPMR-UHFFFAOYSA-N 4-[[5-chloro-4-[3-[(ethylsulfamoylamino)methyl]anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CCNS(=O)(=O)NCC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=2)Cl)=C1 UHKFVZWCALJPMR-UHFFFAOYSA-N 0.000 claims description 2
- NYJUDFVISXHRDX-UHFFFAOYSA-N 4-[[5-chloro-4-[4-[(cyclopropylsulfamoylamino)methyl]-2-methylanilino]pyrimidin-2-yl]amino]-2,6-dimethylbenzenesulfonamide Chemical compound C=1C=C(NC=2C(=CN=C(NC=3C=C(C)C(=C(C)C=3)S(N)(=O)=O)N=2)Cl)C(C)=CC=1CNS(=O)(=O)NC1CC1 NYJUDFVISXHRDX-UHFFFAOYSA-N 0.000 claims description 2
- ZKVXSQYNQKTJOB-UHFFFAOYSA-N 4-[[5-chloro-4-[4-[(cyclopropylsulfamoylamino)methyl]-2-methylanilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C(NC=2C(=CN=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=2)Cl)C(C)=CC=1CNS(=O)(=O)NC1CC1 ZKVXSQYNQKTJOB-UHFFFAOYSA-N 0.000 claims description 2
- DASZAEWGFHELOV-UHFFFAOYSA-N 4-[[5-chloro-4-[4-[(cyclopropylsulfamoylamino)methyl]anilino]pyrimidin-2-yl]amino]-2,6-dimethylbenzenesulfonamide Chemical compound CC1=C(S(N)(=O)=O)C(C)=CC(NC=2N=C(NC=3C=CC(CNS(=O)(=O)NC4CC4)=CC=3)C(Cl)=CN=2)=C1 DASZAEWGFHELOV-UHFFFAOYSA-N 0.000 claims description 2
- GKGTZVXGCNHJSI-UHFFFAOYSA-N 4-[[5-chloro-4-[4-[(cyclopropylsulfamoylamino)methyl]anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Cl)C(NC=2C=CC(CNS(=O)(=O)NC3CC3)=CC=2)=N1 GKGTZVXGCNHJSI-UHFFFAOYSA-N 0.000 claims description 2
- DJNIXIWJIVSPEB-UHFFFAOYSA-N 4-[[5-chloro-4-[4-[(ethylsulfamoylamino)methyl]-2-methylanilino]pyrimidin-2-yl]amino]-2,6-dimethylbenzenesulfonamide Chemical compound CC1=CC(CNS(=O)(=O)NCC)=CC=C1NC1=NC(NC=2C=C(C)C(=C(C)C=2)S(N)(=O)=O)=NC=C1Cl DJNIXIWJIVSPEB-UHFFFAOYSA-N 0.000 claims description 2
- RIQMNYPRUJKDRA-UHFFFAOYSA-N 4-[[5-chloro-4-[4-[(ethylsulfamoylamino)methyl]-2-methylanilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CC1=CC(CNS(=O)(=O)NCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1Cl RIQMNYPRUJKDRA-UHFFFAOYSA-N 0.000 claims description 2
- QWNQDJBIOLYFEG-UHFFFAOYSA-N 4-[[5-chloro-4-[4-[(ethylsulfamoylamino)methyl]anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(CNS(=O)(=O)NCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1Cl QWNQDJBIOLYFEG-UHFFFAOYSA-N 0.000 claims description 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical group CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 2
- 108010036949 Cyclosporine Proteins 0.000 claims description 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 2
- 206010013774 Dry eye Diseases 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 206010020751 Hypersensitivity Diseases 0.000 claims description 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims description 2
- 241001303601 Rosacea Species 0.000 claims description 2
- 102000000551 Syk Kinase Human genes 0.000 claims description 2
- 108010016672 Syk Kinase Proteins 0.000 claims description 2
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 2
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 claims description 2
- 206010046851 Uveitis Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 229960001265 ciclosporin Drugs 0.000 claims description 2
- 229930182912 cyclosporin Natural products 0.000 claims description 2
- 210000002216 heart Anatomy 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 claims description 2
- 229940014456 mycophenolate Drugs 0.000 claims description 2
- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 claims description 2
- 229960004866 mycophenolate mofetil Drugs 0.000 claims description 2
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 2
- 201000004700 rosacea Diseases 0.000 claims description 2
- 229960002930 sirolimus Drugs 0.000 claims description 2
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 2
- 229960001967 tacrolimus Drugs 0.000 claims description 2
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 2
- RXYIYUOOCZCTQP-UHFFFAOYSA-N 5-methylpyrimidine-2,4-diamine Chemical compound CC1=CN=C(N)N=C1N RXYIYUOOCZCTQP-UHFFFAOYSA-N 0.000 claims 1
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims 1
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 230000000735 allogeneic effect Effects 0.000 description 1
- HPNSFSBZBAHARI-RUDMXATFSA-M mycophenolate Chemical compound OC1=C(C\C=C(/C)CCC([O-])=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-M 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14060408P | 2008-12-23 | 2008-12-23 | |
| US61/140,604 | 2008-12-23 | ||
| US12/645,349 US8268851B2 (en) | 2008-12-23 | 2009-12-22 | Compositions and methods for inhibition of the JAK pathway |
| US12/645,349 | 2009-12-22 | ||
| PCT/US2009/069480 WO2010075558A2 (en) | 2008-12-23 | 2009-12-23 | Compositions and methods for inhibition of the jak pathway |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012513480A JP2012513480A (ja) | 2012-06-14 |
| JP2012513480A5 true JP2012513480A5 (https=) | 2013-05-09 |
| JP5485294B2 JP5485294B2 (ja) | 2014-05-07 |
Family
ID=42266455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011543688A Expired - Fee Related JP5485294B2 (ja) | 2008-12-23 | 2009-12-23 | Ｊａｋ経路の阻害のための組成物および方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8268851B2 (https=) |
| EP (1) | EP2370415B1 (https=) |
| JP (1) | JP5485294B2 (https=) |
| CA (1) | CA2745901C (https=) |
| ES (1) | ES2583642T3 (https=) |
| WO (1) | WO2010075558A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| CA2642229C (en) * | 2006-02-24 | 2015-05-12 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US8268851B2 (en) | 2008-12-23 | 2012-09-18 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| WO2014091265A1 (en) * | 2012-12-11 | 2014-06-19 | Aurigene Discovery Technologies Limited | Pyrimidine-2,4-diamine derivatives as kinase inhibitors |
| KR101665301B1 (ko) | 2013-08-07 | 2016-10-11 | 카딜라 핼쓰캐어 리미티드 | 야누스 키나제의 억제제로서 n-시아노메틸아미드 |
| EP3206691B1 (en) * | 2014-10-14 | 2018-09-19 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| US9737683B2 (en) | 2015-05-07 | 2017-08-22 | Aladdin Dreamer, Inc. | Lucid dream stimulator, systems, and related methods |
| US10300240B2 (en) | 2015-05-07 | 2019-05-28 | Aladdin Dreamer, Inc. | Lucid dream stimulator, systems, and related methods |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| WO2020257495A1 (en) * | 2019-06-18 | 2020-12-24 | Purdue Research Foundation | Inhibitors of erythrocyte band 3 tyrosine phosphorylation and uses thereof |
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| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| EP2089369B1 (en) * | 2006-10-19 | 2011-02-02 | Rigel Pharmaceuticals, Inc. | 2,4 -pyrimidinediamine derivatives as inhibitors of jak kinases for the treatment of autoimmune diseases |
| US7947698B2 (en) | 2007-03-23 | 2011-05-24 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| WO2008118823A2 (en) | 2007-03-26 | 2008-10-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US8268851B2 (en) * | 2008-12-23 | 2012-09-18 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
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2009
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- 2009-12-23 WO PCT/US2009/069480 patent/WO2010075558A2/en not_active Ceased
- 2009-12-23 ES ES09835863.3T patent/ES2583642T3/es active Active
- 2009-12-23 EP EP09835863.3A patent/EP2370415B1/en not_active Not-in-force
- 2009-12-23 JP JP2011543688A patent/JP5485294B2/ja not_active Expired - Fee Related
- 2009-12-23 CA CA2745901A patent/CA2745901C/en active Active
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2012
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